N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl ester → N-(2-amino-3-methylbenzyl)-L-alanine ethyl ester

HRID 127570Notes

Reaction equation

HRID 127570 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH3:18])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[N+:15]([O-])=O)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH3:18])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[NH2:15])[CH3:2]

Participants

5

Reactant 2

HCID 53662574N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54551098N-(2-amino-3-methylbenzyl)-L-alanine ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 26.6 g of N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl ester in 100 ml of absolute ethanol was hydrogenated in the presence of 2 g of 10% palladium/carbon. 6.7 liters of hydrogen were taken up in 5 hours. After completion of the hydrogenation, the catalyst was filtered off and the filtrate was evaporated to dryness. There was obtained N-(2-amino-3-methylbenzyl)-L-alanine ethyl ester in the form of a yellow oil; [α]D =-52.6° (c=1% in methanol).

Workup

  1. filtrationAfter completion of the hydrogenation, the catalyst was filtered off
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f3a3d1a3f60b40cdaa251928f761dd7d
Source dataset
uspto-grants-1981_03
Patent number
US04256748

Reaction notes

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